


Guided

by mansikka



Category: Supernatural
Genre: Bottom Dean, Confident Castiel, Exploration, First Time, First Time Bottoming, Getting to Know Each Other, Hand Jobs, M/M, Nervous Dean, Smut, Top Castiel
Language: English
Status: Completed
Published: 2016-03-21
Updated: 2016-03-21
Packaged: 2018-05-28 03:36:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,558
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6313828
Author URL: https://archiveofourown.org/users/mansikka/pseuds/mansikka
Summary: <blockquote class="userstuff">
              <p>Dean's always thought that he took the lead, and that there wasn't really all that much left for him to learn when it came to sex. But then along came Cas. Cas, who has observed humanity for millennia. Cas, who has been learning Dean ever since he pulled him from hell. Cas, who is more than willing to teach Dean a few things, even be patient with him when he's nervous. Dean's about to have a steep learning curve, and is embracing every second of it.</p>
            </blockquote>





	1. Chapter 1

“This is gonna sound all kinds of dumb,” Dean punches out breathily, letting his head fall back a little as he does. “But... I don't... I didn't... I didn't know it'd feel like  _ this _ ,”

 

Cas pauses for a moment and looks down at Dean, his head tilting in curiosity.

 

“This,” Dean emphasises with a roll up of his hips, and Cas' face splits into a grin before he dips his head down and presses his lips into Dean's exposed neck.

 

“Then how did you expect it to feel?” Cas says, his voice halfway between amused and pleased. He rolls his own hips down, his lips curving up into a smirk at the soft groan Dean gives out as he does.

 

“I don't... I don't... I...” Dean stutters out, as Cas' lips on his neck trail a path up behind his ear and are replaced with his teeth back on the way down. “I don't know. I just... feels good... right...”

 

Cas smiles again, nuzzling along his jawline before dropping an open kiss on Dean's mouth as a reward. “I am pleased to hear that I feel 'right', Dean,” he mumbles against his lips, before licking out to taste him.

 

Dean lets out another small gasp and slides one hand through the back of Cas' hair, pulling him down into a hard, bruising kiss, while the other hand slips under Cas shirt and runs languidly up his back. “You do, Cas. You do feel right.  _ This _ feels right,” he says, peppering his words with kisses. “Can't believe I... remind me what we were avoiding this for, Cas?” he whispers, pausing for a second to look Cas straight in the eye.

 

Cas shrugs, smirks, and kisses him again. “It doesn't matter now, Dean. We are doing this now.”

 

Dean grins wide, slides both his hands down to cup firmly around Cas' ass and rocks up against him with a smirk. “Yeah. We are, Cas,”

 

Cas and Dean have been  _ Cas and Dean _ for a few weeks now. And in somewhat unchartered territory for Dean, in something that is most definitely unchartered territory all round, not only are they taking things infinitely slowly – which for Dean, means lots of fully clothed making out like he's a fumbling teenager all over again – but also he's letting Cas take the lead.

 

All the lead: and Dean's not sure there's much  _ letting _ being done really, since Cas has assumed that role without the slightest discussion. For a man in his mid-thirties who's deflowered a woman or two in his time, and been a  _ Mr perfect right now _ more times than he wants to actually ever say out loud, the whole thing is strange.

 

A good kind of strange; Dean's loving all the attention Cas is giving him, and everything that's happening between them feels incredible, even if it is through layers of plaid and denim. But what he's finding he's loving even more, and that is surprising him even more, is how good it feels to relinquish control, to  _ not _ have to be the one taking the lead, to be the one instead being guided.

 

It scares him a bit too, if he's being totally honest. But it's a good kind of scared, and the way Cas ruts down against him between his open legs like he's doing just now, chases away the edge of the fear and replaces it with a warm, buzzing feeling instead.

 

Cas shifts a little, reaching and gripping behind Dean's knees and pulling them upwards so Dean knows to wrap them around him, and stutters out as Cas begins to roll against him in the most lazy of rolls.

 

“You feel 'right' too, Dean,” Cas tells him with a soft sigh and a graze of his teeth against Dean's neck again.

  
Dean is liquid, and loving every second of it.


	2. Chapter 2

**Summary for the Chapter:**

> “I want you, Cas. You've gotta know I want you,”
> 
>  
> 
> Dean's leaning up against the kitchen counter with his hands curled around the edges, staring across at Cas who's standing perfectly still less than three feet in front of him.
> 
>  
> 
> “I believe that you think that you want me, Dean. But how do you know that for yourself?”
> 
>  
> 
> Cas is staring at him hungrily, and Dean's heart is fluttering to see that, and after the conversation they've just had about them taking things a little further, his knees might be a little weak as well.

“I want you, Cas. You've gotta know I want you,”

 

Dean's leaning up against the kitchen counter with his hands curled around the edges, staring across at Cas who's standing perfectly still less than three feet in front of him.

 

“I believe that you think that you want me, Dean. But how do you know that for yourself?”

 

Cas is staring at him hungrily, and Dean's heart is fluttering to see that, and after the conversation they've just had about them taking things a little further, his knees might be a little weak as well.

 

Cas may be the one doing the leading here, but he's also being so very careful of not pushing Dean too far. So he's waiting to see what Dean will say, before deciding on telling him exactly what he wants them to do.

 

That just makes Dean want him all the more.

 

“I know, Cas. I know. I might not have... you know... this... that,” he says, flicking an involuntary glance at Cas' crotch before looking away again and licking his lips nervously. “With... with a guy before. But I know  _ want _ when I feel it. It's like a pressure... a... heat. Right here,” Dean rests a hand low, and splayed out, against his stomach.

 

Cas' eyes drop to Dean's hand, staring. “I want you too, Dean.”

 

Dean nods his head rapidly. “Good. I mean... good. I'm... yeah...”

 

Cas raises his eyes again and gives him a small smile, which Dean can't help but return.

 

“So,” Dean stutters out after a couple of seconds of staring. “What... what do you want? To do?”

 

Cas nods, and takes two paces towards Dean so there is only a small gap between them. With his eyes firmly on Dean's, he lifts his hand from where it is resting against his side, and slowly traces a thumb up Dean's length through his jeans, smiling as Dean stutters forwards.

 

“I want to touch you,” Cas tells him simply, keeping up that thumb stroking as Dean swells thicker. “And I want you to touch me,” he adds.

 

Dean raises a shaky hand, and it seems to take forever before he feels the brush of fabric against his thumb pad. But once he's there, he's trailing a path up Cas, mirroring Cas' thumb on him.

 

Cas' eyes fall closed at Deans' touch, and he gives out a soft  _ mm _ of appreciation. “That feels good,” Cas tells him, leaning forward and kissing him gently.

 

The kiss grows dirtier as they both grow hard, and light fingers up and down their shafts turn to as firm a grip as they can manage through denim. With sliding tongues and choked out encouragement, it isn't long before Cas is pulling back, tangling their free hands together, and asking Dean with nothing more than a look that they move elsewhere.

 

Dean nods, pushes off from the counter, and follows him easily.

 

When they undress each other, Cas' fingers are sure, and steady, but Dean's are fumbling and jittery. His eyes are raking all over Cas as though he doesn't know where to look first, but Cas' gaze is nothing but appreciative, drinking every inch of Dean in.

 

“I don't think I'm ready for... I mean... I wanna touch you, Cas, I do... I just... I don't know how much I can-”

 

Cas cuts him off by cupping his face with both hands and kissing him firmly, pressing himself right up against Dean so that they can both feel exactly how much want is there literally between them. “I want to feel you in my hand, Dean. I want to make you come,”

 

Dean's stuttering and gasping at his words, eyes blown wide with want, and fear, and excited apprehension. “I... I want that too. I mean... I can do that,” he nods rapidly.

 

Cas guides him back to the bed and they scramble across it until they're laying side by side. He raises his hand again to cup against Dean's face, as though he is waiting.

 

Dean's eyes drop down nervously for a second. “I... I guess I never thought... that you'd... that you'd want  _ this _ . And that... I never really thought you'd know what you were doing,” Dean gets out shakily, making Cas' smile about a mile wide.

 

“Your perception of my... knowledge... is... intriguing,” Cas settles for, and Dean knows he is being teased. “I suppose I will just have to prove myself,” he adds, pressing forward for another kiss.

 

Dean lets out a long, ragged breath, the second Cas trails his fingers up along his length and wraps his fingers around him.

 

“How does that feel?” Cas asks him softly as Dean glances down at Cas' hand.

 

“Your hand,” is all Dean manages to stutter out before he's letting his forehead drop against Cas'.

 

“Is there a problem with my hand, Dean?” he whispers with a tinge of amusement.

 

Dean is rapidly shaking his head against Cas', and the second Cas' thumb is stroking over the head of his cock, he's gasping all over again.

 

Dean is thinking to himself how good it feels to have so much of him covered at once, because Cas' hands are decidedly bigger than any he's ever had on him before. And his grip is harder, and rougher, yet seems to already know instantly what feels good to him. And all he can do is arch his head back and moan.

 

Cas grins, as though he knows exactly what Dean is thinking, pressing a soft kiss to his forehead and shifting himself forward. His movement seems to stir something else in Dean, because he's slowly reaching out, stopping midway, then reaching again, until his fingers brush against Cas then hesitantly wrap around him.

 

Cas lets out his own groan of appreciation, and Dean's initial nervousness evaporates.

 

With a look that is a lot more surprised than it probably needs to be, Dean lays his head back on his pillow and holds Cas' gaze. They work each other, learning the perfect grip, and stroke, and tease from the expressions on each other's faces, and it's all unhurried, and imperfect, and better than anything Dean's been letting himself imagine.

 

He's thrusting into Cas' hand unable to control it, breath getting shallower and eyes getting wider, and when Cas pushes on his hip to urge him to roll on to his back, Dean goes without complaint. He lets go of Cas when he nudges his hand away, and lets his knees splay at Cas' urging. His eyes are down on Cas' hand around him, then up at his face, and there's nowhere he can look for long enough.

 

Cas is relentless, smiling and kissing praise into Dean and shifting ever closer, his own cock leaking over where it's pressing into Dean's thigh.

 

It only takes the slightest change of grip and Dean is breathing out Cas' name over and over, and his hands clench and unclench as he bucks up without any control left at all. And then he's arching up a little, moaning out low, and long, and staring down at himself open-mouthed as he's painting himself in thick streaks.

 

Cas smiles down at him all kinds of pleased, stroking lightly until Dean's shifting with overstimulation.

 

“I liked doing that, Dean,” Cas tells him, still smirking, leaning forward and pressing a soft kiss to his lips. Dean chases a kiss back that is a lot harder, as though in gratitude, and seconds later is reaching out for Cas all over again.

 

But Cas is shifting, kneeling, leaning forward to grind them together for a second until their balls are brushing against each other's, which makes Dean gasp out to feel. Cas picks up Dean's hand and guides him to wrap it around himself, steadying himself with his hands on Dean's hips and encouraging him on with soft grunts telling Dean exactly how much he's enjoying his hand on him.

 

Cas thrusts into Dean's hand, purposely angled so that their bodies glance off each other, and Dean's giving out tiny moans of appreciation himself. It isn't long before Cas is falling forward and bracing himself against the bed, looking down between them at Dean's hand with a groan.

 

When he comes, Cas arches against Dean, making a further mess of Dean's already splattered chest. He looks down at Dean triumphantly for a moment, before leaning forward to kiss him briefly, then rolling to the side with a huff of contentment.


	3. Chapter 3

**Summary for the Chapter:**

> “I'm sorry for being such a girl about this,” Dean mumbles, and instantly looks up at the click of disapproval Cas is giving him.
> 
>  
> 
> “I do not understand why being nervous about a new experience is something that is purely a feminine attribution,” Cas tells him with a stern look. “Or why being 'a girl' in this situation is somehow something derogatory.”

“I'm sorry for being such a girl about this,” Dean mumbles, and instantly looks up at the click of disapproval Cas is giving him.

 

“I do not understand why being nervous about a new experience is something that is purely a feminine attribution,” Cas tells him with a stern look. “Or why being 'a girl' in this situation is somehow something derogatory.”

 

Dean winces, instantly chastised, and reaches out his fingers to tangle around Cas'.

 

“Sorry. I didn't mean anything by it,” he says, grimacing to himself. “It's just a... kneejerk kind of expression.”

 

“It is an outdated one,” Cas tells him firmly again, raising a shrewd eyebrow.

 

For a moment, Dean feels cornered, like he always does when he's said something wrong. But soon Cas is relenting, rolling his eyes a little but smiling as he nudges himself in between Dean's legs where he's sitting, and bending down to kiss him.

 

“There is nothing wrong with being nervous about this, Dean.”

 

Dean purses his lips together and nods, trying to believe that.

 

It's a few more weeks down the line for their relationship, and while they've grown skilled with their fingers on each other, they've still been moving the physical side of things between them along at a slow pace.

 

Yesterday, when Cas had trapped their leaking cocks against their stomachs and rolled down on Dean until they both came, Dean had allowed himself to wonder what it might feel like to have something more.

 

Because speaking was a thing they did with each other now, instead of loaded silences and possible misunderstandings, Dean had said exactly that. How he thought he might be ready to take that further step between them. How he wanted to find out what it might feel like to have Cas actually inside him.

 

The moment the words were passed his lips, Dean realised just how badly he really, really wanted that to happen.

 

Cas' pupils had dilated to hear it, and Dean had watched as he'd swallowed repeatedly before he could speak. His kisses had been loaded with want, and promise, and carefully they agreed that it would happen sometime soon.

 

Very soon.

 

Telling himself they weren't going to make a big deal out of this, Dean had mumbled a suggestion about maybe getting a room somewhere so they had privacy for it. Not that it was a big deal, or that they were making an event out of it or anything like that. Not out loud, anyway.

 

He must have looked nervous when he'd told Sam that he and Cas were going away for a couple of days, because Sam's comments about a  _ dirty mid-week _ were kept to an almost bare minimum.

 

And as he'd packed up an overnight bag, Dean's eyes had fallen on to the bottle of lube he'd brought with blushing cheeks at the pharmacy, and he'd had to drop down on the bed, clutching his head in his hands, and tell himself not to be such an idiot.

 

But here they were now, in a hotel much nicer than their usual accommodation. Nothing fancy, because that wasn't their style, but with matching furniture, and soft towels, and walls that had a solid look about them that promised to keep any noises they might be making from escaping through.

 

Cas uses the tangle of their fingers to guide Dean to his feet, dropping them to cup his face and pull him closer for a gentle kiss. Dean sighs into it, wrapping his arms around Cas' waist and dropping his eyes closed as Cas presses right up against him.

 

Undressing each other has become something of a cherished routine between them: with every revealing of skin comes a brushing of lips or hands, leaving both of them gasping for more.

 

As always, Cas is the one who's guiding them to lay down on the bed, and as his hand runs up from Dean's knee, to his thigh, and rests lightly on his hip as he leans over him, the look he gives Dean is nothing but heated.

 

Dean reaches out a hand and wraps it around Cas' cock, as Cas begins a trail of kisses over his skin. He doesn't miss a spot; neck, cheek, ear, only pausing to give the occasional thrust into Dean's hand and follow it up with a soft groan.

 

Cas reaches down and gently grips around Dean's wrist, bringing it and his other hand to lie flat on the bed at waist level, and pins them there. He's leaning completely over Dean and kneeling between his legs, and begins a trail of kisses down his chest.

 

When he's at eye level with Dean's cock, he glances up for a second then licks his tongue out and over his head, smirking at the gasp Dean gives him in response. Cas wants to suck him into his mouth entirely, but already knows Dean's body well enough not to overstimulate him all in one go.

 

So he moves on, reining kisses over his stomach, hips, and down his thighs, before pressing another kiss into each kneecap. With light fingers, he lifts Dean's knees, encouraging him to lay his feet flat against the bed.

 

Cas presses lightly on Dean's inner thighs until they're parted as comfortably as he can get them. Only then does he look up and over Dean, and the look Cas gives him then makes Dean's cock twitch just to see how much he's wanted.

 

With another kiss to his thigh, Cas leans up for a moment to reach for the bottle of lube Dean's got next to him on the pillow. He kneels back between Dean's legs, looking down at the bottle in thought before uncapping it.

 

“You know, Dean,” he begins, drizzling the gel onto his fingers, “the human body does secrete enough fluid for this not to be necessary,”

 

He raises his eyes to Dean and smirks. “And I know exactly what to do to you to make you... leak,” he says, with a grin that says he knows exactly what he does to Dean when he says things like that.

 

As if to prove that, Dean's cock twitches again, and Cas reaches out to swipe up the precum there, smiling again as Dean judders at his touch.

 

“I know,” Dean manages to choke out. “I know. But...”

 

“I am not complaining, Dean. I imagine this will feel very good,” he says quietly, scissoring his fingers in mid air as he warms the gel. “Are you ready?” he asks then, glancing back up to Dean.

 

Dean sucks in a breath and nods rapidly, swallowing hard. His eyes are fixed firmly on Cas' fingers as they dip between his legs, and as Cas uses one hand to hold him gently open, Dean's juddering breath makes Cas pause, and look back up.

 

“Dean,”

 

“It's okay. It's good. Just... nervous,” Dean chokes out, nodding at him and opening his legs a little wider.

 

Cas looks back down, and slowly presses the tip of his finger in until the first knuckle disappears, glancing up again. Dean is nodding, so he slides in a little further, and a little more, until Dean's blowing out a shallow breath.

 

Dean flicks him a smile, telling him to keep going, so Cas does exactly that, pressing his finger in as far as it can go. He stays there, letting Dean get used to the feel of it for a moment before withdrawing it. He pumps it in again slowly, drawing it back out, then slowly in again, and it's on the third stroke in that Dean gives a surprised moan that says he's liking it.

 

Cas glances up, receiving a smile that encourages him on. He continues stroking in and out of Dean whilst holding eye contact, and Dean's breathing becomes heavier as he watches. When Cas withdraws his finger this time and he feels him pushing in two at once, the strange, burning pleasure feeling it shoots through him has Dean dropping his head back against the pillow in a thud.

 

Cas keeps stroking into him as though he's in no hurry at all, smiling at the noises Dean is making. It's when he presses in and around Dean's walls, scissoring his fingers and glancing them against his prostate, that Dean lets out a long, low grown, and arches up, pressing himself down on Cas' fingers with a grunt.

 

By the time Cas has drizzled more lube on his fingers and is sliding three fingers in and out of him at a steady pace, Dean is a whimpering mess, writhing and shaking his head back and forth on his pillow as his cock strains erect and leaking.

 

“Do you think you are ready, Dean?” he asks, and Dean's grabbing for him as though he's trying to drag him up.

 

Cas shifts on to his knees again from where he'd sat cross legged as he'd worked Dean open, and with his fingers still pumping into Dean, he awkwardly uncaps the lube and slicks himself up. He kneels forward, lining himself up between his fingers to press bluntly against him, looking at Dean again to make sure he is absolutely sure.

 

When Dean nods, Cas slowly withdraws his hand, and he's sure he can hear Dean's heart thudding. He presses his hole open with his thumbs and rests his cock head there, but doesn't move any further until Dean nods again.

 

Cas rolls his hips only a touch, and only until his head slides inside him. He bites back the groan he feels, because Dean's stuttering and tensing beneath him, and Cas doesn't want to rush him. Cas waits, until he feels Dean relax enough for him to push in again.

 

He gets a little further in, and Dean's scrambling for him, calling out his name in a panic and gripping hard on to his forearms. So Cas stops, slides his hands up and on to Dean's stomach and rests them there, waiting again. He smiles when Dean unscrews his eyes and stares up at him in astonishment, and in another moment he feels the give that says he can press in again.

 

Dean's breathing out shallower and shallower with every inch that Cas is filling him, and when Cas is fully inside him, Dean lets out a soft, choked cry that immediately has Cas tensing up with worry.

 

Cas leans forward to kiss Dean softly. “Are you okay?” he mumbles into his lips, then pulls back enough so that he can see all of his face, to make sure that Dean is going to be honest about what he's thinking, and feeling.

 

Dean nods his head frantically, shakes it a little, and laughs at himself. “I don't know, Cas. It feels... I don't know how it feels,” he says, and it sounds to Cas as though he's holding his breath. “Can we wait a minute?” he asks haltingly, his fingers fluttering anxiously at Cas' sides.

 

“Of course, Dean. We will take as much time as you need,” Cas reassures him, before smiling again, shifting so that he can brace himself against the bed better, and starts a long, leisurely kiss, that soon has Dean sighing out relaxed and reaching his arms up to loop around his neck.

 

“I think you can move now,” Dean whispers against his lips after a little while, and Cas waits another moment before doing just that.

 

Cas can't stop the groan escaping this time as he rocks himself out and slides all the way back in, because Dean feels so good, and everything feels so right, that there's no way to not show how much he's enjoying this. And after a few, purposefully slow thrusts, Dean's giving that soft, surprised moan of appreciation he'd given earlier, letting his hands drift down Cas' back and rest around his hips.

 

Cas rocks into him and does his best to keep it steady, and Dean's breaths are coming out more and more erratic and surprised. When Cas shifts how he's kneeling, Dean lets out a stifled bark of a grunt, and Cas smirks, knowing exactly whatm and where, his head is hitting. He winks at Dean, and Dean gives a small burst of laughter to see it, then begins rolling his hips up in time with Cas', still with that look of utter amazement on his face.

 

And soon they're a writhing, moaning mess, lips pressed into skin and glancing against one another as Cas reaches between them and slowly strokes Dean's cock. Dean lets out a noise that sounds a lot like a keening whimper, and he's glancing down at Cas' hand around him and up at his face like he's about to burst with every sensation he's experiencing at once.

 

Cas slows his pace a touch because of Dean's expression, and now Dean really is whimpering; grabbing him impossibly closer and pleading for Cas to keep fucking him just  _ there _ .

 

So Cas is relentless, and Dean is choking out, tensing up, chanting his name hoarsely as his orgasm builds, and builds, and builds to an intensity where there's a roar in his ear and a wave rushing through him, and he's coming in a long arch that feels like it starts somewhere up at his throat and ends down at where Cas is deep inside him. Cas moans out to see it, and uncontrollably starts pounding into him harder, falling forward, growling out Dean's name until he stiffens, arching hard against him, before spilling himself in Dean with a deep, rumbling groan.

 

Cas falls forward on Dean's chest, and Dean gives a little huff at the weight of him, before pressing an absent kiss into the side of his head. He wraps his arms tightly around him, holding Cas firmly in place for a moment as his heart continues racing, before Cas is sliding himself out and falling down heavily beside him.

 

The moment Cas hits the bed, he's opening his arms wide to Dean and whispering, “Come here,” then wrapping his arms securely around him as Dean buries himself into his chest. Cas rubs soothing circles into his back and repeatedly drops kisses down on the top of his head, until he feels the tremble in Dean subside, and knows that he is calm.

 

Cas waits a little longer, until Dean raises his head and looks up at him, his mouth curving up with a smile that is both shocked, and happily sated.

 

It's at that point that Cas grins at him, leaps up with a lot more energy than Dean thinks he should be feeling, and definitely doesn't feel himself, and returns with a wash cloth to gently clean him down. Then he's crawling back beside Dean, pulling him into his arms again, and kissing him firmly on the mouth, all while still grinning wide.

 

“Don't know what you're looking so smug about,” Dean grumbles, although his grin has spread just as stupidly.

 

“Yes, you do, Dean,” Cas tells him, raising an eyebrow as he smiles once more. Then presses forward and claims another kiss.

  
  



End file.
